2,6-Lutidine → 3-Methoxy-4-methylbenzaldehyde

HRID 615511Notes

Reaction equation

HRID 615511 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6](Cl)=[O:7].N1C(C)=CC=CC=1C.[H][H]>[Pd].C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH:6]=[O:7]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 27595843-Methoxy-4-methylbenzoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 47150953-Methoxy-4-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.0 g (27.08 mmol) of 3-methoxy-4-methylbenzoyl chloride, 4.0 ml (34.34 mmol) of 2,6-lutidine and 400 mg of 10% palladium on carbon in 40 ml of THF was rapidly stirred under an atmosphere of hydrogen until no more hydrogen was taken up. Filtration and extraction with ethyl acetate gave title compound as a light yellow oil.

Workup

  1. filtrationFiltration and extraction with ethyl acetate

Sources & evidence

ORD record
ord-2206dd495341406a86ac888b68687a31
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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